Tag Archives: Apple Mail

Troubleshooting, debugging Apple Mail connections

For troubleshooting connectivity issues with Apple Mail and an IMAP type account:
Ensure Mail is not running. This presumes you(r account) is using SSL/TLS for security (thus port 993) as you should be.
While logged in as the user in question, use the Terminal to issue:

/Applications/Mail.app/Contents/MacOS/Mail -LogSocketErrors YES -LogActivityOnHost your.mailserver.com -LogIMAPErrors YES -LogActivityOnPort 993 &> ~/Desktop/ConnectionLog.txt

Quit Mail from within the app after a minute or less. You can watch for activity (eg: to complete) in the Activity window.

For an Exchange account (which requires and uses Microsoft’s EWS),
ensure Mail is not running, and while logged in as the user in question, use the Terminal to issue:

/Applications/Mail.app/Contents/MacOS/Mail -LogHTTPActivity YES -LogEWSAutodiscoveryActivity YES >& ~/Desktop/MailEWS.log

Use the Window menu in Mail to bring up the Activity window, and wait for connection(s) to complete. Or give it a minute.
Quit Mail from within the app, and check the log.

Expanding the functionality of Apple Mail

Apple Mail by itself is one of the best email-management applications on the market. It’s taken a while to get there, but as of 10.6 it’s a robust mail client that supports everything from the old POP3 standards up to the current version of Microsoft Exchange. Its built-in tools for managing email also make it one of the most flexible email clients available today: The abiltiy to have both server-side and local folders; the combination of having a unified inbox for multiple accounts and the ability to view said inboxes separately; the ability to take one or more accounts offline temporarily while leaving the others active with ease; and so on.

And, of course, it comes with the Mac OS at no extra cost. Always a plus.

But it has a few things missing that seem unimportant at a glance, but which can improve workflow and productivity immensely. Fortunately, there are some third-party software developers who have written add-ons for Mail. I’m going to take a quick look at three of them.

First, there’s DockStar (which I’ve personally been using for the past five or six years), from the Ecamm Network. It expands on a function already built into Mail – showing an unread message count. But where Mail just shows you the total number of unread emails, DockStar adds the ability to show (in customizable icons) the unread mail count in up to five separate mailboxes. It shows these icons both on Mail’s Dock icon, and in the menu bar, making it easy to tell – at a glance – if the email that just arrived is one you need to look at right away or not. It’s also good for showing you when mail arrived while you were away from your desk, and for reminding you that you have messages waiting for your attention.

Second, there’s a program I’ve been using for a few months called Herald. At a glance, it adds Growl support to Mail, adding an Entourage-like pop-up notification that new mail has arrived. But it goes a lot deeper than that. Herald’s pop-up, unlike Entourage’s, only comes up if you’re in an application other than Mail, and shows you not just the subject of the email but also the sender, recipient, and body of the message (stripped to plain text). And if that’s not useful enough, it includes a row of buttons that allow you to delete the message, mark it as spam, mark it as read or reply to it from the Herald pop-up window, allowing you to take care of a priority email without having to switch to Mail manually – Herald does it for you, then when you’re done it takes you back to the application you were working in before-hand.

And if THAT’S not enough, it allows you to choose which mailboxes it pops up new messages for – so if you’re subscribed to a mailing list (and have a Rule set up sending them to their own folder as they come in) and don’t need to see messages from it right away, you can tell Herald not to show new messages in that folder.

Finally, a program I only found recently called FlagIt!, from TastyApps. It does one simple thing: It allows you to flag messages (and color the entire message row) in different colors. I used to leave messages marked unread so they’d be highlighted, reminding me I needed to deal with them. With FlagIt!, I can color something red for high priority, making it stand out when I glance at Mail, which is much, much better. This is one of those functions that doesn’t even occur to most people until it’s mentioned to them, but which then becomes indispensable once used.

As a side-note, I can’t speak highly enough about TastyApps’ support. I initially had a problem with FlagIt! that they went to great lengths to help me solve, even though it took a couple of weeks to find the source of the problem. And when I found that Mail was using far more RAM than it should while running it, they took the time to identify the memory leak as being theirs and will be patching it in the next version of the software.

So there you have it: Apple Mail, with expanded functionality to improve your work-flow. There are more add-ons available, these are just the three I’ve found most useful – so if you feel like something’s missing from Mail, look around…someone might already have written an add-on for it.

— Josh